Efficient and Green Method for the Synthesis of 1,5‐Benzodiazepine and Quinoxaline Derivatives in Water

References

• Grieco , P. A. 1998 . Organic Synthesis in Water London : Blackie Academic and Professional .
   Google Scholar
• Anastas , P. T. and Williamson , T. C. 1996 . Green Chemistry , ACS Symposium Series 626 Washington, DC : American Chemical Society .
   Google Scholar
• Li , C.‐J. and Chan , T.‐H. 1997 . Organic Reactions in Aqueous Media New York : Wiley .
   Google Scholar
• Schutz , H. 1982 . Benzodiazepines Vol. 2 , p. 240 Heidelberg : Springer .
   Google Scholar
• Smalley , R. K. 1979 . Comprehensive Organic Chemistry Edited by: Barton , D. and Ollis , W. D. Vol. 4 , 600 Oxford : Pergamon .
   Google Scholar
• Landquist , J. K. 1984 . Comprehensive Heterocyclic Chemistry Edited by: Katritzky , A. R. and Rees , C. W. Vol. 1 , 166 – 170 . Oxford : Pergamon .
   Google Scholar
• Randall , L. O. and Kappel , B. 1973 . Benzodiazepines Edited by: Garattini , S. , Mussini , E. and Randall , L. O. 27 New York : Raven Press .
   Google Scholar
• Sarges , R. , Howard , H. R. , Browne , R. G. , Label , L. A. and Seymour , P. A. 1990 . 4‐Amino[1,2,4]triazolo[4,3‐a] quinoxalines. A novel class of potent adenosine receptor antagonists and potential rapid‐onset antidepressants . J. Med. Chem. , 33 : 2240
   PubMed Web of Science ®Google Scholar
• Gomtsyan , A. , Bayburt , E. K. , Schmidt , R. G. , Zheng , G. Z. , Perner , R. J. , Didomenico , S. , Koenig , J. R. and Turner , S. 2005 . Novel transient receptor potential vanilloid 1 receptor antagonists for the treatment of pain: Structure‐activity relationships for ureas with quinoline, isoquinoline, quinazoline, phthalazine, quinoxaline, and cinnoline moieties . J. Med. Chem. , 48 : 744
   PubMed Web of Science ®Google Scholar
• Seitz , L. E. , Suling , W. J. and Reynolds , R. 2002 . Synthesis and antimycobacterial activity of pyrazine and quinoxaline derivatives . J. Med. Chem. , 45 : 5604
   PubMed Web of Science ®Google Scholar
• Jaso , A. , Zarranz , B. , Aldana , I. and Monge , A. 2005 . Synthesis of new quinoxaline‐2‐carboxylate 1,4‐dioxide derivatives as anti‐mycobacterium tuberculosis agents . J. Med. Chem. , 48 : 2019
   PubMed Web of Science ®Google Scholar
• Essaber , M. , Baouid , A. , Hasnaoui , A. , Benharref , A. and Lavergne , J.‐P. 1998 . Synthesis of new tri and tetraheterocyclic systems: 1,3,‐Dipolar cycloaddition of nitrilimines on 2,7‐dimethyl‐4‐phenyl‐3H‐1,5‐benzodiazepin . Synth. Commun. , 28 : 4097
   Web of Science ®Google Scholar
• El‐Sayed , A. M. , Abdel‐Ghany , H. and El‐Saghier , A. M. M. 1999 . A novel synthesis of pyrano(2,3‐c)‐, 1,3‐oxazino(2,3 b)‐, 1,2,4‐triazolo(3,4‐b)‐, oxazolo(2,3‐b)‐, furano(3,2‐c)‐, and 3‐substituted‐(1,5)benzodiazepin‐2‐ones . Synth. Commun. , 29 : 3561
   Web of Science ®Google Scholar
• Zhang , X. Y. , Xu , J. X. and Jin , S. 1999 . Cycloaddition of benzoheteroazepine III: Reaction of 2,3‐dihydro‐1H‐1,5‐benzodiazepines with dichlorocarbene and stereo‐structures of products . Chin. J. Chem. , 17 : 404
   Web of Science ®Google Scholar
• Brock , E. D. , Lewis , D. M. , Yousaf , T. I. and Harper , H. H. (The Procter and Gamble Company USA) . WO Patent 9951688 . 1999 .
   Google Scholar
• Haris , R. C. and Straley , J. M. U.S. Patent 1,537,757 . 1968 . Chem. Abstr. 1970, 73, 100054w, File date 1999
   Google Scholar
• Herbert , J. A. L. and Suschitzky , H. 1974 . Synthesis of heterocyclic compounds. Part XXIX. Substituted 2,3‐dihydro‐1H‐1,5‐benzodiazepines . J. Chem. Soc., Perkin Trans. 1. , : 2657
   Google Scholar
• Morales , H. R. , Bulbarela , A. and Contreras , R. 1986 . New synthesis of dihydro‐ and tetrahydro‐1, 5‐benzodiazepines by reductive condensation of o‐phenylenediamine and ketones in the presence of sodium borohydride . Heterocycles , 24 : 135
   Web of Science ®Google Scholar
• Jung , D. I. , Choi , T. W. , Kim , Y. Y. , Kim , I. S. , Park , Y. M. , Lee , Y. G. and Jung , D. H. 1999 . Synthesis of 1,5‐benzodiazepine derivatives . Synth. Commun. , 29 : 1941
   Web of Science ®Google Scholar
• Balakrishna , M. S. and Kaboudin , B. 2001 . A simple and new method for the synthesis of 1,5‐benzodiazepine derivatives on a solid surface . Tetrahedron Lett. , 42 : 1127
   Web of Science ®Google Scholar
• De , S. K. and Gibbs , R. A. 2005 . Scandium(III) triflate as an efficient and resusable catalyst for synthesis of 1,5‐benzodiazepine derivatives . Tetrahedron Lett. , 46 : 1811
   Web of Science ®Google Scholar
• Curini , M. , Epifano , F. , Marcotullio , M. C. and Rosati , O. 2001 . Ytterbium triflate promoted synthesis of 1,5‐benzodiazepine derivatives . Tetrahedron Lett. , 42 : 3193
   Web of Science ®Google Scholar
• Pozarentzi , M. , Stephanatoe , J. S. and Tsoleridis , C. A. 2002 . An efficient method for the synthesis of 1,5‐benzodiazepine derivatives under microwave irradiation without solvent . Tetrahedron Lett. , 43 : 1755
   Web of Science ®Google Scholar
• Jarikote , D. V. , Siddiqui , S. A. , Rajagopal , R. , Daniel , T. , Lahoti , R. J. and Srinivasan , K. V. 2003 . Room temperature ionic liquid promoted synthesis of 1,5‐benzodiazepine derivatives under ambient conditions . Tetrahedron Lett. , 44 : 1835
   Web of Science ®Google Scholar
• More , S. V. , Sastry , M. N. V. and Yao , C.‐F. 2006 . Cerium (IV) ammonium nitrate (CAN) as a catalyst in tap water: A simple, proficient and green approach for the synthesis of quinoxalines . Green Chem. , 8 : 91
   Web of Science ®Google Scholar
• Bhosale , R. S. , Sarda , S. R. , Ardhapure , S. S. , Jadhav , W. N. , Bhusare , S. R. and Pawar , R. P. 2005 . An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using molecular iodine as the catalyst . Tetrahedron Lett. , 46 : 7183
   Web of Science ®Google Scholar
• Venugopal , D. and Subrahmanmyam , M. 2001 . Single‐step synthesis of 2‐methylquinoxaline from 1,2‐phenylenediamine and 1,2‐propanediolover modified HY zeolites . Catal. Commun. , 2 : 219
   Google Scholar
• Goswami , S. and Adak , A. K. 2002 . The first microwave assisted regiospecific synthesis of 6‐substituted pterins . Tetrahedron Lett. , 43 : 8371
   Web of Science ®Google Scholar
• Zhao , Z. , Wisnoski , D. D. , Wolkenberg , S. E. , Leister , W. H. , Wang , Y. and Lindsley , C. W. 2004 . General microwave assisted protocols for the expedient synthesis of quinoxalines and heterocyclic pyrazines . Tetrahedron Lett. , 45 : 4873
   Web of Science ®Google Scholar
• Wu , Z. and Ede , N. J. 2001 . Solid phase synthesis of quinoxalines on SynPhase™ Lanterns . Tetrahedron Lett. , 42 : 8115
   Web of Science ®Google Scholar
• Attanasi , O. A. , Crescentini , L. D. , Filippone , P. , Mantellini , F. and Santeusario , S. 2003 . Improved synthesis of substituted quinoxalines from new N˭N‐polymer‐bound 1,2‐diaza‐1,3‐butadienes . Synlett , 8 : 1183
   Google Scholar
• Singh , S. K. , Gupta , P. , Duggineni , S. and Kundu , B. 2003 . Solid phase synthesis of quinoxalines . Synlett , 14 : 2147
   Google Scholar
• Robinson , R. S. and Taylor , R. J. K. 2005 . Quinoxalie synthesis from α‐hydroxy ketones via a tandem oxidation process using catalyzed aerobic oxidation . Synlett , : 1003
   Web of Science ®Google Scholar
• Raw , S. A. , Wilfred , C. D. and Taylor , R. J. K. 2004 . Tandem oxidation processes for the preparation of nitrogen containing heteroaromatics and heterocyclic compounds . Org. Biomol. Chem. , 2 : 788 – 796 .
   PubMed Web of Science ®Google Scholar
• Raw , S. A. , Wilfred , C. D. and Taylor , R. J. K. 2003 . Preparation of quinoxalines, dihydropyrazines, pyrazines and piperazines using tandem oxidation processes . Chem. Commun. , : 2286 – 2287 .
   PubMed Web of Science ®Google Scholar
• Santelli , M. and Pons , J.‐M. 1995 . Lewis Acids and Selectivity in Organic Synthesis Boca Raton, FL : CRC Press .
   Google Scholar
• Schinzer , D. 1989 . Selectivities in Lewis Acid Promoted Reactions Dordrecht, , The Netherlands : Kluwer Academic .
   Google Scholar
• Fringuelli , F. , Pizzo , F. and Vaccaro , L. 2001 . Lewis acid catalyzed organic reactions in water. The case of AlCl3, TiCl4 and SnCl4 believed to be unusable in aqueous medium . J. Org. Chem. , 66 : 4719
   PubMed Web of Science ®Google Scholar
• Kobayashi , S. 1994 . Rare earth metal trifluoromethanesulfonates as water‐tolerant Lewis acid catalysts in organic synthesis . Synlett , : 689
   Web of Science ®Google Scholar
• Kobayashi , S. 1991 . Lanthanide trifluoromethane sulfonate as stable Lewis acids in aqueous media. Yb(OTf)3 catalysed hydroxymethylation reaction of silyl enol ethers with commercial formaldehyde solution . Chem. Lett. , : 2187
   Web of Science ®Google Scholar
• Kobayashi , S. and Hachiya , I. 1994 . Lanthanide triflate as water tolerant Lewis acids. Activation of commercial formaldehyde solution and use in the aldol reaction of silyl enol ethers with aldehydes in aqueous media . J. Org. Chem. , 59 : 3590
   Web of Science ®Google Scholar
• Kobayashi , S. and Ishitani , H. 1995 . A novel mannich type reaction in aqueous media. Lanthanide triflate‐catalyzed condensation of aldehydes, amines and vinyl ethers for the synthesis of β‐amino ketones . J. Chem. Soc., Chem. Commun. , : 1379
   Google Scholar
• Kobayashi , S. , Hachiya , I. , Ishitani , H. and Araki , M. 1993 . Scandium trifluoromethanesulfonate (Sc(OTf)3) as a novel reusable Lewis acid catalyst in aldol and michael reactions . Synlett , : 472
   Web of Science ®Google Scholar
• Hachiya , I. and Kobayashi , S. 1993 . Aqueous reactions with a Lewis acid and an organometallic reagent. The scandium trifluoromethane sulfonate‐catalyzed allylation reaction of carbonyl compounds with tetraallyltin . J. Org. Chem. , 58 : 6958
   Web of Science ®Google Scholar
• Loh , T.‐P. and Chua , G.‐L. 2006 . Discovery of indium complexes as water tolerant Lewis acids . Chem. Commun. , : 2739
   PubMed Web of Science ®Google Scholar
• Gogoi , P. and Konwar , D. 2006 . An efficient and one pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon‐nitrogen bonds in water . Tetrahedron Lett. , 47 : 79
   Web of Science ®Google Scholar